Little Mistakes
by Katie Coleman
Summary: After a big night out, Dean comes home to find an unexpected message on his voice mail.So, the boys are on the road again, and Dean is in for the shock of his life. Set sometime after Route 666
1. Chapter 1

**Disclaimer: If taking characters that belong to a TV show, and putting them in a story I've made up all on my own with my very own sub-plot without actually owning them or the people that own the show is a sin, then forgive me Father for I have sinned. Several times, actually.**

_Title:_ "Little Mistakes"

_Summary: _Dean returns to their hotel suite after a big night out, only to find that the ex-love-of-his-life has some _very_ big, life-changing, news for him and Sam.

_Rating:_ T

_Warnings: _Language, possibly themes (y'know, horror, death and sorts) & Character Death...

_Re-make:_ Yup, I re-wrote this following chapter (1)

_Author:_ NaturallySupernatural

_Beta-Reader(s):_ None.

-

Cassie paced frantically up and down her hallway. She'd been putting this moment off for days, but enough was enough. After she'd heard the news she'd known she should call him straight away, but she just couldn't. How would he take it? What if he didn't want anything to do with her anymore? Cassie sighed in desperation and tried to calm her raging nerves. Her stomach was tying itself in knots, almost enough to make her sick.

'It's now or never.' she told herself, as she reached for her cell phone and dialled in his number. The phone rang several times, and with each ring she dreaded him picking up even more, but she knew she had to tell him now. Eventually it rang through to his voice mail;

'This is Dean Winchester. Please leave a message after the tone, if it's an emergency text me with your co-ordinates.'

_Damn_ Cassie bit her lip. 'Uh- Hi Dean. It's Cassie... look, could you please call me back as soon as you get this, I have something to tell you.'

She pressend the 'end call' button on the keypad and placed her phone back down again. Well, at least she'd called him now; she just hoped he'd bother to ring her back.

-

Sam Winchester sat on the end of the cramped hotel bed, tears streaming down his face leaving a clean patch of skin in amongst the dirt.

'I miss you.' he'd managed to stutter, as he let the memories of Jess roll in, even though it made his heart ache more than anything else in the world. He remembered his first date with her, all the dates after that, what his friends had said about her, how much they liked her, when she moved in, and then shopping for the rings. He'd had this beautiful ring picked out, with a golden band and a sparking god-knows-how-many-caret diamond on the top. When got back from his hunting trip with Dean was meant to be the happiest day of his life; he was planning to propose to the love of his life that night. Instead, his heart got torn apart into tiny pieces, to delicate to ever be put back together again, and he left without saying a proper goodbye. That'd the thing he regretted the most- leaving before her funeral.

_Ring... ring... ring... ring... _

He jumped as Dean's phone went off on the nightstand. He reached to answer it, but then retreated as he changed his mind. If it was important, they'd ring back. His brothers' voicemail would kick in, anyway. He sighed, the tears coming to a halt as he leant back on the bed and closed his eyes.

-

Dean stumbled through the hotel room door sometime past 4 o'clock the next morning, a goofy expression plastered all over his face. At just one glance Sam could tell his brother had consumed _way_ to much alcohol.

'Dude, where have you been?' he gawked at Sam, before hurridley dashing to the hotel suite bathroom.

'Brothers!' Sam huffed, shaking his head.

-

Dean sat on the cold bathroom floor, running his pale hand through his hair. _Damn_ he thought to himself. _Shouldn't have had that last tequila. Or the one before that. Or the one before that..._

He leant back against the wall, it's tiles almost the exact same shade as his own face. He closed his eyes and tried to ignore the throbbing pain in he's head, willing it to go away, but it refused to be ignored and became even stronger. He was tired, and his effort over the last half hour had taken every morsel of strength out of his body.

'Dean!' He heard Sammy's persistent tapping on the door.

'I'm still alive, dude. No need to worry.' he groaned, fighting back the urge to spill the contents of his stomach over the floor once again.

'Okay.' He heard Sam's footsteps walking away from the door and back into the main room of the hotel suite.

-

'Feeling better bro?' Sam laughed as his brother emerged from the bathroom three hours later.

'Yeah much. Thanks for the concern, bitch.' Dean frowned, his head still throbbing impatiently.

'Jerk.' Sam retorted, handing his brother a steaming hot cup of coffee. Dean pursed his lips into a weak smile. 'Thanks'.

'Your phone rang while you were _out_ last night.' Sam continued.

'Oh yeah. Who was it?' Dean asked, the coffee already making him feel a bit more alive.

Sam shrugged. 'Dunno, didn't answer it.' He grabbed his brothers' cell phone off of the nightstand and handed it to him.

'Thanks.' Dean took his phone and dialled in the voicemail number. 'You have one new message.' The recorded voice told him.

_'Uh- Hi Dean. It's Cassie... look, could you please call me back as soon as you get this, I have something to tell you.'_

-

**A/N:** Okay, so I wasn't really happy with this chapter originally, so I re-wrote it. Don't know what I'll do about the next one, but please review all the same! Thanks, and sorry to anyone who read this story prior to this update and liked the original verision, but I thought it look and sounded a little 'novice-y' in parts (which it probably still does, lol!) so I changed it. Thanks!


	2. Chapter 2

**Disclaimer: If taking characters that belong to a TV show, and putting them in a story I've made up all on my own with my very own sub-plot without actually owning them or the people that own the show is a sin, then forgive me Father for I have sinned. Several times, actually.**

_Title:_ "Little Mistakes"

_Summary: _Dean returns to their hotel suite after a big night out, only to find that the ex-love-of-his-life has some _very_ big, life-changing, news for him and Sam.

_Rating:_ T

_Warnings: _Language, possibly themes (y'know, horror, death and sorts) & Character Death...

_Re-make:_ Yup, I re-wrote this following chapter (2)

_Author:_ NaturallySupernatural

_Beta-Reader(s):_ None.

-

**Previously:**

_'Your phone rang while you were out last night.' Sam continued._

_'Oh yeah. Who was it?' Dean asked, the coffee already making him feel a bit more alive._

_Sam shrugged. 'Dunno, didn't answer it.' He grabbed his brothers' cell phone off of the nightstand and handed it to him._

_'Thanks.' Dean took his phone and dialled in the voicemail number. 'You have one new message.' The recorded voice told him._

_'Uh- Hi Dean. It's Cassie... look, could you please call me back as soon as you get this, I have something to tell you.'_

-

'Uh, Dean, are you okay man?' Sam asked, concerned.

'Yeah, Sammy, I'm fine.' Dean lied, placing the phone back down on the nightstand.

Sam shrugged. 'Okay, well I'm going to have a shower now you're out of the bathroom, alright?'

Dean nodded absent mindedly, too caught up in his own thoughts to really care what his brother was doing.

When he heard the reassuring _click_ of the lock on the bathroom door, he picked his phone back up, dialled in Cassie's number and hit the 'call' button.

'Hey Dean!' Her voice travelled down the crackly phone line.

'Cas', I uh- got your message?' He said nervously.

'Oh, that...' she paused. 'Um, Dean I think that it's best you come down here and hear this in person.' she told him.

Dean nodded. 'Okay, Cassie, but I don't when I can get down there-'

'It's important, Dean.'

Dean sub-consciously bit his lip as he heard the running water in the shower come to a halt. 'Okay, but I've got to go now. I'll get down there A.S.A.P.' He looked over his shoulder to see if Sam was coming out of the door yet.

'Okay, Dean, see you.'

_Click._ Dean flipped the phone shut and placed it carefully in his pocket. He listened intently as the bathroom door swung open and Sam stepped out. 'Hope you didn't use up all the hot water, jerk.' he said.

Sam smiled as he put his duffel bag down on the bed. 'Back to your old self I see.'

'As always.' Dean nodded.

'So, who rang?' Sam questioned his older brother as he walked over to the small kitchenette to make himself another coffee.

'Oh, just some stupid telephone company," Dean shrugged. 'Wanted to upgrade our phones to a 'Premium Plan' they said, whatever the hell that is.'

Sam nodded, although he didn't really believe Dean's excuse. Someone had left that message... someone _important_. Maybe it was dad? No, their father hardly ever rang, let alone left a voice mail. Too risky for John. People, _things_, could pick up where you were by the background noise. Whoever it was, it wasn't him.

Sam poured his coffee in silence, watching his brother walk over to the single bed and begin cramming his clothes into his bag.

'What are you doing?' He asked, confused.

Dean turned to look at him. 'Oh, didn't I tell you?' he bent down to pick their road map up off the floor. 'We're leaving.'

-

'Dude, where _are_ we going?' Sam demanded, throwing his duffel bag in the trunk of the Impala.

'Cape Girardeau.' Dean replied, matter-of-factly.

Sam raised his eyebrows. 'Isn't that where Cassie lives?' he asked.

Dean looked up at his brother, arched his eyebrows, cocked his head to the side and replied 'Yes, your point being?'

Sam shrugged. 'Nothing. Just _why_ are we going there?'

The eldest Winchester brother opened the drivers' side door and stepped in, ignoring his brother. When Sam was seated safely and comfortably in the passenger's seat, he started the engine and took off towards the highway.

The two sat in silence for a while, Sam wondering _who'd_ left the voiceamail on Dean's phone, and Dean wondering _why_ she'd left it.

Sam broke the silence with a cough. 'Dude, you never answered my question.' he said.

Dean glanced over at his brother. 'And what was that?' he asked.

'Why are we going to Cape Girardeau?' Sam repeated.

'Because,' Dean turned to look at his brother again. 'That's where Cassie lives.'

-

**A/N:** Okay, so I re-wrote this chapter, too. Hope it's better, and BTW, the third is on it's way!


	3. Chapter 3

_Previously;_

_Sam broke the silence with a cough. 'Dude, you never answered my question.' he said._

_Dean glanced over at his brother. 'And what was that?' he asked._

_'Why are we going to Cape Girardeau?' Sam repeated._

_'Because,' Dean turned to look at his brother again. 'That's where Cassie lives.'_

…

'We're… going to see Cassie?' Sam asked in amazement, shocked that Dean would _actually_ want to see Cassie after their previous… departure.

'Yeah, got a problem with that, College Boy?'

Sam shook his head. 'No, just wondering…'

'Wondering _what_ Sam?' Dean demanded, tapping the steering wheel impatiently.

Sam turned to look at his brother, his expression paved with confusion. '_Why_ are we going to see Cassie?'

Dean threw his head back against the seat and sighed. 'I don't know, Sam.'

'Oh my god…' Sam muttered, shaking his head as a look of realization crossed his face. 'Oh my god…'

…

Finally, it was all beginning to come together in Sam's mind. The phone call… Cassie… Dean dragging him along to visit her… But, it couldn't be. Could it?

'Dean, you do realize what this means, don't you…?'

With no desire at all to even _think _about what 'this means', the elder shot his brother a threatening glance to silence him.

'_If he doesn't shut up…'_

'Sam…' He warned, turning back towards the road.

Sam was quiet, and Dean held the victory over his brother. 'Just don't say _anything_ is you can't say anything _good_.' He told him.

'Whatever man. Your mess.'

…

Pulling his car into the all-too-familiar driveway, Dean had never felt so nervous in his life. Not when their Dad had left him to look after Sammy during a hunt, not even when the Wendigo had him strung up in the rafters of its 'cozy little home.' _Never_.

Had it not been for Sam standing next to him as the walked up the steps to her house, Dean might've turned and run back to the Impala and sped off towards the nearest motel he could find. But Sam _was_ there, and he _had_ to do this.

Glancing down at his elder brother, Sam took it upon himself to knock on the door.

_Knock… Knock… Knock…_

Seconds later, they heard footsteps approaching the door.

'C'mon… Sam, if we run now, we can still get away before she opens the--'

Cassie smiled, taking in the boys' appearance. 'Dean! Sam! You look well. Come in!' She smiled, ushering them through the door and into the living room.

'So,' she said, taking a seat on the lounge chair opposite Dean. 'How are you?'

'Good. You?' Dean replied nervously.

Cassie smiled and nodded. 'Okay, enough with the small talk.' She turned to Sam. 'Uh, do you mind if I just have a word with your brother… in _private_?'

Sam looked from Cassie, to Dean, and back again, unsure. 'Uh, okay.'

'Go wait in the car, Sammy.' Dean commanded. Frowning, Sam rose to his feet and walked towards the door.

Once his brother was clearly out of ear-shot, Dean turned to face Cassie. 'So?'

'Dean, this is big. I don't know how you'll react, but here it is- I'm pregnant. And… it's yours.'

…

Sam met Dean as he walked out of the house. 'What? What did she say?'

'Nothing.'

'Dean. She said something, what was it?'

'I don't want to talk about it Sammy.' Dean replied angrily as he marched towards the car.

'Dean…'

'Sam. Shut up.'

…

A/N: Okay, I think that was a fairly good note to leave it on, to continue tomorrow. I promise! I know, I didn't update for ages, and I'm truly sorry, but life got in the way a bit, along with several computer crashes and major writers block. Tell us what you think! 


	4. Chapter 4

_Previously: _

_Sam met Dean as he walked out of the house. 'What? What did she say?'_

'_Nothing.'_

'_Dean. She said something, what was it?'_

'_I don't want to talk about it Sammy.' Dean replied angrily as he marched towards the car._

'_Dean…'_

'_Sam. Shut up.'_

…

The drive home was silent, as Dean sat pondering his future, and Sam sat beside him, silently wishing that Dean would tell him what was going on.

When they arrived back at the hotel, Dean slammed the car door and raced inside, leaving Sam sitting in the passenger seat alone. What Dean hadn't realized, though, was he had also left his cell phone unguarded on the dashboard of his beloved Impala, and this was something that he would later come to regret.

Sam smirked and reached for the phone, because, hell, if Dean wasn't going to tell him what was up, he knew someone who would.

"Hey, Cassie, it's Sam Winchester." He paused. "Yeah, Dean's brother."

Another long pause as he listened to the voice on the other end of the line.

"Look, Dean's been acting… very strange since we got back. Did- uh, did something happen?"

Sam's brow creased in concentration. "Oh, I see… Thank you." He flicked the phone shut, replaced it in its position on the dashboard and got out of the car.

…

Inside the hotel room, Dean sat stiffly on his bed, rubbing his head with the palm of his hand.

"God…"

There was a light tapping at the door, and Dean looked up as his younger brother entered the room. He rose to his feet quickly, hiding all evidence of his emotions.

"Dean?" Sam said softly. "It's okay, I know."

Sam made his way over to where his older brother stood, and laid a hand on Dean's shoulder in an effort to comfort him. Dean runs a hand through his shaggy, brown-blonde hair.

"You know what? I'm screwed."

…

"Hey Dad, it's Sam. Look, Dean… he's in a bit of trouble. He needs you, more than ever. We're in Cape Girardeau. Get here as fast as you can…"

Sam sighed and clicked the phone shut. Not like he was really expecting John to answer his call, anyway, but… well, it would have been nice.

Dean approaches his brother from behind, freshly showered and changed.

"So, are we going, or not?" He asked enthusiastically.

"Going… where?" Sam turned to look at his brother, confused.

"The bar!" Dean grinned.

"Why?"

Dean shrugged. "Gonna be here for a while by the looks of it, might as well make our selves known among the locals."

Sam frowned at his brother's impulsiveness for a moment, and then replied; "Okay…"

Dean hit Sam on the shoulder playfully. "At a boy!"

…

A/N: Sorry that update was short (again). I'm just about to write another chapter to upload a little later on… Hope you enjoyed! Review!


	5. Chapter 5

Warnings for: Language and… pink elephants!

_Previously:_

_Dean shrugged. "Gonna be here for a while by the looks of it, might as well make our selves known among the locals." _

_Sam frowned at his brother's impulsiveness for a moment, and then replied; "Okay…" _

_Dean hit Sam on the shoulder playfully. "At a boy!" _

…

John leant back against the tray of his sleek black truck as he listened intently to the message that had been recorded to his voicemail.

"_Hey Dad,"_ John recognized the harsh tone of his youngest son's voice at once, and smiled to himself. It had been a while…

"_It's Sam. Look, Dean… he's in a bit of trouble. He needs you more than ever. We're in Cape Girardeau. Get here as fast as you can…"_

His pleasure in hearing Sam's voice again wore off almost immediately after 'Dean's in trouble'. What sort of trouble? He sighed and swung his duffel bag into the back of the vehicle. Walking around to the side of the truck, he opened the driver's side door.

"It's Dean. Sam says he's in trouble, they want me there." He said.

"Ain't nothin' you can do, John. You have to stick with the job." Came a gruff reply form the passenger's seat.

John hesitated for a moment, considering his options before stepping into the car and slamming the door closed.

"I guess you're right…"

…

Sam sat uncomfortably at a table inside the hot, stuffy bar and flipped through their father's journal as his brother flirted with anything that possessed a pair of legs, and downed more beers than Sam was willing to count. That's the way it always is, the way it always had been. When Dad had left to hunt something, Dean was always the first one into the whisky, even when he wasn't old enough to drink, and Sam held no doubt that it been the same way after he himself had left for college. And now he watched on as Dean once again drank himself into a state of comfort.

He felt a hand brush against his shoulder and span around in his seat to face a man, balding and about thirty years older than Sam.

"'Scuse me," He said gruffly. "I got a message for ya."

Sam raised his eyebrows in surprise. "Me?"

"No, the pink elephant in the seat next to ya. Yeah, you, kid. A guy told me to tell you that he's waitin' for ya outside."

Sam looked down in confusion. "He… is?"

The other man rolled his eyes. "You're not as bright as you look, you know that?" He huffed, before walking away to join three other men standing by the pool table.

…

Dean smiled up at the blonde… she was pretty, and she was tall… God was she tall. But, then again, that could have just been the- what? Eight beers, going on nine?- talking, he really didn't know. Really didn't care.

"So…" She whispered. "Where do you work?"

Dean smirked. "All over the place, sweetheart, sometimes I don't even know myself."

The blonde- Bianca- nodded approvingly. "What do you do there?" She asked.

"All sorts of things," Dean replied. "Maybe we can talk about that over another beer…"

Bianca smiled down at him, and he winked back up at her. "Oh, I don't know… you seem fairly wasted over there." She replied.

Dean shrugged and looked down at his glass, deflated. "Am I?"

"Oh my God," Bianca peered over Dean's shoulder and towards the exit of the bar. "Look at that idiot!"

Dean swiveled around on his chair and followed Bianca's gaze, just in time to see Sammy exiting the bar, barstool and two beers in hand.

"Shit." Dean turned back around to face Bianca. "Excuse me, but I have to go."

…

Outside of the stuffy bar, the cold night air hit Dean like a rush of blood to the head. He had to hold on to the door handle for a few more seconds to correct his balance, before walking on again.

Dean jogged out of the bar behind him.

"Dude! What the hell are you doing?" He called out.

"He's out here, Dean. He's watching us…" Sam replied, distractedly.

"Wow," Dean muttered as he slowed to a walk beside his brother. "You downed more alcohol than I gave you credit for, college boy."

Sam stopped in his tracks and turned to face his elder brother.

"You don't believe me, do you Dean? You don't believe me!"

…

"_He's out here, Dean. He's watching us…"_ Does this mean our boys could be in a little more trouble than they thought?

Another short update, but I'll have more coming soon, I promise  Reviews are appreciated.


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